A process for producing cyanonorbornene by using dicyclopentadiene and acrylonitrile is described in Patent Documents 1 and 2, for example.
Patent Documents 1 and 2 disclose a method of recovering acrylonitrile and cyclopentadiene or dicyclopentadiene which are non-reactive raw materials included in a reaction product when producing cyanonorbornene by consecutively reacting cyclopentadiene or dicyclopentadiene and acrylonitrile and reusing thereof as a raw material. Examples and the like of Patent Documents 1 and 2 disclose that the reaction system includes methyl bicyclononadiene.
Patent Document 3 discloses that tetrahydroindene has low reactivity in the Diels-Alder reaction and a high decomposition temperature, and thus is mixed in a raw material compound for circulative reuse and accumulated in the system. In addition, since tetrahydroindene has an impact on reaction, there is disclosed a method of reducing the compound.
Patent Document 4 discloses a process for producing an amine compound by using cyanonorbornene or a process for producing an isocyanate compound by using the amine compound.